Following contentious US policies on Ukraine and Gaza, President Donald Trump has turned his attention to Iran, seeking to reopen negotiations with America’s long-standing adversary.

But the path to a potential agreement is strewn with obstacles.

Iran’s nuclear programme, with enrichment levels nearing weapons-grade capacity, remains a key point of contention.

Trump’s decision to withdraw from the 2015 nuclear deal during his first term, coupled with his “maximum pressure” campaign, has left Tehran deeply distrustful of Washington’s intentions.

“I would rather negotiate a deal. I’m not sure that everybody agrees with me, but we can make a deal that would be just as good as if you won militarily,” Trump said in a recent Fox News interview.

Yet, Trump’s conciliatory tone was laced by threats: “If we have to go in militarily, it’s going to be a terrible thing for them.” He also warned that “something is going to happen very soon,” repeating the phrase for emphasis.

“The other alternative is we have to do something because you can’t let them have a nuclear weapon," he added. 

Iran denies that it is developing a nuclear weapon, but it has continued to enrich uranium to higher levels, particularly after the previous Trump administration withdrew from the JCPOA, killing the Obama-era deal with Iran. 

Trump portrays himself as a master negotiator, ramping up pressure on Tehran — but Iran hasn’t budged. Iran’s response to ‘Trump’s threats’ has been indifferent.

Iran’s supreme leader Ali Khamenei dismissed negotiations with a “bullying government,” without addressing the US directly. 

Meanwhile, the response of Iran’s moderate president, Masoud Pezeshkian, was blunt: “Do whatever the hell you want.”

Iran’s UN mission, however, left a door slightly ajar.

“If the objective of negotiations is to address concerns vis-à-vis any potential militarization of Iran’s nuclear program, such discussions may be subject to consideration,” the mission said in a statement.

The confusion surrounding Trump’s overture did not help matters.

Iranian Foreign Minister Abbas Araghchi claimed no letter had been received from Trump. Yet, Anwar Gargash, diplomatic adviser to the president of the UAE, reportedly delivered the letter to Tehran on Wednesday, underscoring the fragmented state of communication.

The Trump administration is weighing a plan to intercept and inspect Iranian oil tankers at sea. That invoked an international accord of 2003 Proliferation Security Initiative designed to curb the spread of weapons of mass destruction.

Can both sides negotiate?

“The fact that Trump publicly announced it beforehand makes the entire situation dubious,” says Ghoncheh Tazmini, an Iranian-Canadian political analyst. “He wants to strike a deal, but setting this kind of tone from the outset reflects the nature of the engagement he seeks.”

Trump’s letter “signals an effort to reopen nuclear negotiations,” says Dr Daria Daniels Skodnik, a political scientist and former Deputy Commandant at the NATO Defence College in Rome.

She highlighted the inherent contradictions in Trump’s approach: “This aligns with his long-standing ‘maximum pressure’ strategy, designed to force Tehran into concessions through sanctions and deterrence.”

“While the letter’s contents remain undisclosed—along with any potential role by Putin in facilitating it—Trump publicly framed Iran’s choice: negotiate or face military action,” Dr Skodnik tells TRT World. 

Dr Skodnik also pointed out allegations that Iran’s Revolutionary Guard Corps (IRGC) plotted to assassinate Trump last year, further souring the prospects of direct diplomacy, making it an uphill task.

“Getting Iran to the negotiating table will be difficult,” Tazmini echoes the same sentiment. “The military-security-intelligence faction within the supreme leader’s camp remains highly sceptical of any engagement with the Trump administration,” she adds.

Khamenei himself labelled Trump’s letter a “deception,” reinforcing Tehran’s instinct to resist US pressure rather than give in.

But Iranians participated in a China-sponsored meeting in Beijing alongside Russians to seek how to revive the 2015 nuclear deal, which will expire in October if not renewed. 

“We still hope that we can seize the limited time we have before the termination date in October this year, in order to have a deal, a new deal so that the JCPOA can be maintained,” said China’s UN Ambassador Fu Cong on Wednesday, prior to a special UN Security Council meeting on Iran’s nuclear programme.

“Putting maximum pressure on a certain country is not going to achieve the goal,” the ambassador added, referring to Trump’s threats to Iran. 

Can Iranian setbacks force Tehran to a deal?

Iran’s regional influence has waned since October. Hezbollah, its Lebanese ally, has been battered by Israeli strikes, while Syria’s Assad regime—another Iranian ally—collapsed under a sudden opposition advance in December.

“Iran’s regional deterrence has weakened, leaving its position increasingly vulnerable,” says Dr Skodnik. “Israel has systematically dismantled much of Iran’s air defence network, heightening the risk to its nuclear sites.”

These setbacks might eventually push Tehran towards diplomacy—but not from a position of perceived weakness. “Iran may prefer to endure hardship rather than negotiate under duress,” Skodnik adds.

What would it take to make a deal?

For any agreement to be viable, “regional or EU sponsorship” would be essential, says Dr Skodnik. “Gulf states like Saudi Arabia, the UAE, and Qatar, with their evolving ties to Tehran, could act as intermediaries.”

“A phased economic relief-for-nuclear-restrictions framework may hold more promise than broad ultimatums,” she says.

She adds that if the US shifts its strategy toward “restricting Israeli pre-emptive strikes on Iranian soil in exchange for nuclear de-escalation” might encourage Tehran to “recalibrate its nuclear ambitions”. 

According to recent IAEA estimates, Tehran’s nuclear enrichment has reached 60% purity, which is much higher than the Obama-era nuclear deal limits. Nuclear weapon production requires a purity level of 90 percent.  

“Despite its weakened position—or perhaps because of it—Iran should not be underestimated. A military strike on its nuclear facilities remains a high-risk option that could escalate rather than resolve the crisis,” adds Dr Skodnik.